A remarkable enhancement of the rate of ester thiolysis by synthetic amphiphile vesicles

IM Cuccovia, FH Quina, H Chaimovich

Index: Cuccovia, Iolanda M.; Quina, Frank H.; Chaimovich, Hernan Tetrahedron, 1982 , vol. 38, # 7 p. 917 - 920

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Citation Number: 46

Abstract

Cationic surfactant vesicles accelerate the rate of thiolysis of p-nitrophenyl octanoate by n- heptylmercaptan by several million fold in the pH range from 4 to 6, providing an efficient system for ester thiolysis in aqueous solution that is functional even at pH4, ie more than 6 pH units below the pKa of the SH group. Analysis of the data in terms of an ion exchange formalism implies that this rate acceleration is due primarily to concentration of the ...